


Little Fantasies

by TheWeirdyMcWeirderson



Category: Supernatural
Genre: Biting, CHeerleader!Reader, Coach!Dean, Dirty Talk, Dirty Thoughts, F/M, Kissing, Rough Sex, Slightly - Freeform, Smut, Swimming Coach!Sam, Teasing, dom!Dean, possessive!dean
Language: English
Status: Completed
Published: 2016-03-21
Updated: 2016-03-21
Packaged: 2018-05-28 02:45:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,155
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6312298
Author URL: https://archiveofourown.org/users/TheWeirdyMcWeirderson/pseuds/TheWeirdyMcWeirderson
Summary: <blockquote class="userstuff">
              <p>Reader and the Winchesters have to go undercover in a high school to solve a case and the Reader has to go as a cheerleader, which provides Dean an excuse to live out his fantasy.</p>
            </blockquote>





	Little Fantasies

**Author's Note:**

> Let me know what you guys think about it, and as usual, Enjoy! *kisses*

"I hate you, both of you!" You folded your arms across your chest, glaring daggers at the younger Winchester for the awful plan he'd just come up with, while Dean sat there chuckling.

"I don't understand what the problem is, (Y/n)! Everyone always says you look younger!" You sighed, that was true, but that didn't mean you wanted to go back to high school. You hated that place.

A string of murders had started to take place in a small town in South Dakota, and it looked like the creature had a liking for popular kids, which you couldn't really blame it for; most of them were jerks.

"C'mon, babe, it want take more than a week, it won't be that bad!" Your eyes shifted on your boyfriend, who you noticed was enjoying this situation way too much for your liking.

"Won't be that bad?! Do I have to remind you how mean those little monsters can be?" Both brothers shook their heads, smiling at you as you huffed in annoyance.

"You're a hunter, (Y/n)! Besides, you're hot, they won't be mean to you, sweetheart" Dean pulled you to sit on his lap, brushing some hair behind your shoulder to peck your cheek.

You fought back the smile that was going to show on your lips, pouting and rolling your eyes, "You'll be joining the cheerleading team and the case'll be over before it has even started!"

A laugh erupted from your chest at the absurdity of Sam's statement, that was until you locked eyes with him and noticed the seriousness in them, "Are you-I'm gonna...what?"

"The victims so far have been either cheerleaders or the jocks from the football and swimming teams, so each one of us is gonna infiltrate between these kids, and since you're a former cheerleader, you won't have any problem!"

You frowned for a second, you'd never told Sam you'd been on the cheerleading team during high school; you'd never told anyone a part from Dean and you suddenly understood why he seemed so happy about this case.

You remembered when you'd first started dating, and you were sitting with Dean on the hood of the Impala, sharing stories about your past.

You'd told him how you were forced to join the cheerleading team to get some extra credits and you'd never forget the wide grin that spread on his lips, "Do you still have the uniform?"

Dean'd pulled you close and nuzzled your neck when you'd told him it was probably still buried somewhere with the clothes you didn't wear anymore, "You think it still fits?"

You'd shrugged, telling him you weren't really that interested into reminiscing those days, and he'd pouted but dropped off the topic, not wanting to upset you.

Now, as you stared at the excited, boyish grin plastered on his face, you began to realize that maybe he had a thing for cheerleaders, and if you were right about your assumption, you were ready to take full advantage of it.

After discussing with the boys all the tiny details of the plan and Sam taking care of all the bureaucratic stuff, you all went to work on your respective covers.

Dean was going to be the football coach, and you were dying to see him sporting that uniform, while Sam was going to be the swimming team coach, and you could only imagine how the girls were going to drool over him.

You put on the uniform Sam had gotten you, pulling your hair up in a high ponytail to keep it out of your face, before wearing your sneakers and grabbing your rucksack.

As soon as you stepped out of the bathroom, Dean's eyes were on you. His jaw practically hit the floor when he saw you in the little outfit and his mouth right down watered at the sight.

"(Y/n), you look-you're...damn!" He licked his full lips a few times before he forced his eyes up to yours, "Stop drooling all over the place, Winchester, and go change or we'll be late!"

It was almost painful for him to tear his gaze away from you, but he was forced to when Sam'd told him you were going to leave in ten minutes.

They'd dropped you off a block away to avoid raising suspicions, and you'd walked to the high school, all the way tugging down the skirt that barely covered your bottom.

Classes had gone pretty smoothly, the teachers had made you introduce yourself to your new 'classmates' and before you new it, it was practice time.

You reluctantly walked to the football field, where everybody had told you the cheerleaders had their practice, and sure enough they were there, giggling and twirling their hair as they stretched.

Your eyes however, were immediately drawn to Dean, who was wearing a pair of pants that did wonders for his sculptured ass, and a form fitting t-shirt with the logo of the team.

You scanned the way his muscles looked under the tight fabric, slowly biting your lower lip, "He's hot, isn't he?" You looked at the girl standing beside you, her appearance resembling your own, even though she was younger.

"Sorry, what?" She flashed you a warm smile, gesturing to Dean, "The new football couch, he's hot, huh? They say he's friends with the swimming coach, can you imagine them in the same room I would certainly faint!"

You chuckled at the dreamy look on her face; you had to admit she was right, the Winchester brothers had been blessed with an incredible set of genes, and coupled with their big hearts, they were undoubtedly real life princes.

Brushing off the thought, you followed the girl, Jamie, who introduced you to the rest of the girls. You soon understood you were wrong in your assumptions about them.

Sure, there were a few girls who'd fit your description perfectly, but most of them were nice and down to earth, instantly accepting you in their team and making you feel at ease.

You'd been undercover for three days, and Sam had finally figured out you were dealing with a shapeshifter, now you just had to figure out what it looked like, and the job was done.

You were going over the routine with the rest of the guys, before you had to try the jumps. You took a five minutes break, during which you spoke with Ollie, the guy who was going to partner up with you.

He picked you up, to feel how much you weighted and when he was more than sure he could lift you up easily, he put you back on your feet and grabbed a bottle of water for each of you.

"He's staring at you!" You turned to face Jamie with a questioning eyebrow raised, and she giggled gesturing to where the football team was practicing, "Coach I-could-make-you-come-with-a-wink, is staring at you...again!"

You flashed her a smile, shrugging your shoulders, "He's probably interested in the routine will be using to cheer his players, that's all" She shook her head at you, smiling and going to her respective partner.

You knew why Dean was staring at you, he'd been doing nothing else everytime you were wearing the cheerleading outfit. He just stared, licking his lips and scanning your body up and down, never saying a word.

Everyone took their places, Ollie standing behind you with his hands on your waist, ready to pick you up when the time was right, and you smirked, noticing how Dean's eyes were still on you.

You could only guess the possessive thoughts that were swirling in his head. He hated when a guy dared to even look at you, and you knew it was taking all of his self control to restrain himself from walking over and showing Ollie you were his.

Your tongue poked from between your lips, and you slowly traced your upper lip, before pulling the lower one between your teeth, and you knew Dean was growling.

He always did, everytime you'd lick your lips while staring directly at him, he would lose it; drop whatever he was doing and pick you up, marching to his room to show you what happened if you teased him like that.

Now, however, he couldn't do it. He was forced to watch you and do nothing about it, watch you in that revealing attire that only served to add to his arousal.

Dean cursed under his breath, eyes locked on your parted lips as thoughts of where he wanted them to be filled his mind, before he shifted his gaze back down over your body. 

The skirt did nothing to cover your ass, that perfect ass of yours that gave him all sorts of dirty thoughts when he saw you bending over, and that tight top, he was glad you wore a bra when he'd asked you to, otherwise he wouldn't have let out of the motel.

That outfit was both a blessing and a curse. A blessing cause it gave him the chance to watch his gorgeous girlfriend dressed as a cheerleader, and he was hoping for a little show afterwards.

And a curse, cause he hadn't considered the amount of horny teenagers who'd get to drool over his girlfriend, and then jerk off in their rooms at the thought of her, and that was killing him.

Dean drew in a deep breath, surely letting his temper get the best of him wouldn't solve the case for you; he had to focus on who the shifter might be, and then he could have you all to himself.

When practice was over, you grabbed your cell and found a text from Sam, telling you that he'd taken care of the shifter and that it was a kid from the drama club, taking the killings of the play a little too literally.

A grin stretched on your lips, when you read the second part of the text where he told you to inform Dean and that he'd be waiting for you at the motel. You grabbed your stuff and quickly made your way to the coach's office.

You knew Dean would be done in about ten minutes or so, that's why you decided to wait for him in his office, ready to act on that little fantasy he seemed to have.

The doorknob twisted, and you took in a deep breath as Dean opened the door and froze in his spot. He turned and checked that no one was around, before making his way in and locking the door behind his back.

"(Y/n), what are doing here? What if someone saw you?" You licked your lips watching him as his eyes locked on them, "I know I shouldn't be here, Coach Winchester. I'm sorry, but I really needed to see you!"

His Adam's apple bobbed when he swallowed, the way you'd addressed him sending shivers down his spine, and just then he seemed to notice the way you were sitting on his desk.

Your legs were crossed, showing off your soft thighs that the miniskirt did nothing to hide; your hands were on either side of your body as you leant back and pushed your chest forward, allowing him the best view.

"You know, Miss-" He turned to look at you, pretending not to know your name, and you felt your stomach fill with butterflies, "(L/n), Miss (L/n)!" He smirked, a smug, confident smirk that had you trembling under his gaze.

"Well, Miss (L/n), you could get into some serious trouble if someone catches you here..." You nodded your head, eyes locked on his green ones as you bit down on you lower lip.

"I know, I'm sorry, Coach! But I really, really needed to see you!" Dean sat down on his chair, and you hopped off of his desk, turning around and placing your hands on it, to face him and give him a nice look at your cleavage.

You'd removed your bra as soon as you'd walked into his office, and from the growl that left his lips, you knew he'd noticed, "I'm right here now, why don't you tell me what the matter is?"

"You see..." You circled the desk, until you were leaning against it, with your thigh mere inches away from his hand, and you could see how his fists clenched, "...I've been having some serious trouble focusing lately"

"Really? And what do you think the cause of that might be?" A slow smile was spreading on his lips, one that you hoped wouldn't show on your face as well, "Oh, I know what the cause is...and I happen to know what the solution could be too"

He was grinning now, a grin that made your heart skip a beat, "What's that?" You hopped on his desk again, your bare thigh brushing his hand, and lightly spread your legs as you bent forward and let your forefinger trace down his chest.

"You!" Your voice had dropped to a sultry whisper and you saw as he bit down on his lip, "I'm your coach, (Y/n), you shouldn't be saying this kind of stuff, don't you think?"

He pushed his chair back a little, giving you more room and you immediately shifted until you were sitting right in front of him, your feet on either side of his chair to keep him caged, "But I want you, Coach!"

Dean swallowed, your little, innocent act was having its tool on him, and you knew it, "I think you should leave, (Y/n), before I do something that will get us both in a lot of trouble, me especially!"

You pouted your lips, giving him your best puppy dog eyes and spread your thighs a little wider, "Please, Coach, I've been doing nothing but think of you all day long, and I'm really, really wet for you! I promise I won't tell anyone"

Dean groaned, his eyes darting to the blue underskirt you were wearing and he wondered if you had any panties underneath, but from the way you were looking at him, he was ready to bet that you didn't.

"I'm sorry, (Y/n), I can't do this!" He was about to stand up, but you pushed him back on the chair, "C'mon, Coach! I know you want me, too! I can see the way you look at me during practice. You like it when I bend over for you, don't you?"

You got up and turned around, bending with your hands on his desk and pushing your ass out for him, hearing a deep, animalistic growl reverberate from within his chest and setting your body on fire.

"Please, Coach Winchester, I promise to be a good girl!" And that did it, his hands landed on your ass and he gave it a firm squeez, groaning when you pushed back into him.

"No one will know?" You shook your head as he stood up, towering over you and adding to his authoritative stance, "I won't tell anyone, Coach, please..." You pushed back again, this time to be met by his straining erection.

"See what you did to me, little girl? I think you should take care of that!" You moaned your agreement, turning around to face him and ready to drop on your knees, but Dean stopped you, grabbing the back of your neck and crashing his lips on yours.

You moaned in the kiss as he bit down on your lower lip, nipping and sucking at it and adding to your already messy state, "That's not what I want, little girl! I want you to sit back, spread your legs for me and show me just how much you want me to fuck you!"

You groaned at his words, breathlessly nodding your head and going to remove your clothes, "Keep the skirt on!" You did as he asked, and only removed the underskirt, before climbing on the desk and spreading your thighs for him.

Moisture was coating your core, glistening under the light and showing Dean just how much you were affected by him. He smiled as you separated you folds for him, whimpering as the cold air hit your most intimate parts.

"See, Coach, see how wet I am for you?" You slightly rolled your hips, hoping to get a reaction from him cause you were in desperate need of release, "Oh, I see alright! Such a dirty girl, aren't you? Getting all hot and bothered for your Coach!"

You bit down on you lip, staring into his big, green eyes and nodding your head as an answer to his questions. Dean brought his forefinger to your centre, slowly dragging it between your outer lips and coating it with your juices.

His eyes stayed on yours and you saw him clenching his jaw with the strength he was using to retrain himself, as his fingertip gently grazed your clit, making you buck your hips against his hand and release a wanton moan.

"This what you want, little girl?" You let your head rest on the desk, drawing in a deep breath, "Yes, Coach...please!" He chuckled then, a deep, low chuckle that never failed to get you dripping for him.

"What's the matter, (Y/n)? Guys your age are not enough for you?" His finger teased your entrance, just barely dipping in, before he resumed his teasing all over your core, "No, I want you, Coach, want your big cock inside me, please!"

Dean groaned at your words, pushing his digit inside your dripping entrance and stopping, "You feel that, little girl, feel how your walls are clenching around my finger? You want it bad, don't you?" You groaned, trying to move your hips, but he placed his other hand on your stomach stopping you.

"Coach Winchester, I need more, please, please fuck me!" He bent down, covering your body with his sturdier one, nuzzling your neck and placing a soft kiss there, before whispering in your ear, "I'll give you exactly what you need, sweetheart!"

You moaned at his promise, widening your thighs to give him more room as he unbuttoned his pants and pushed them down his legs along with his boxers, "Ready, little girl?" You nodded, grabbing a fistful of his tee and bringing him down on you.

"Yes, yes, take me Coach! Fuck me so hard everyone will know what a dirty girl I am!" You mumbled the words against his lips, your eyes locked on his green ones and you could see as they darkened in lust.

He thrust into you without a warning, your juices making him slide right into you, and he grinned down at you when you threw your head back and moaned his name, momentarily forgetting your little act.

"You like that? Like having my cock buried deep inside you, little girl?" You clawed at his back, ending up gripping his t-shirt for levarage, "Yes, God, yes! I love it! L-love the way y-you're stretching my l-little pussy, Coach! Aahhh-fffuck you're so big!" 

Dean groaned when your walls tightened on him, forcing him to stop for a second and draw in a deep breath before he slowly pulled out of you, until just the tip was in; a loud whine leaving your lips.

"Look at that, your tight, little pussy is dripping for me, little girl!" You moaned, rolling your hips and teasing him, hoping to get a reaction out of him but failing as he pulled out completely.

His cock pressed onto your clit, and he dragged it up and down your core, making you purr in delight at the friction it was providing on your swollen bundle of nerves, "Can you hear that, (Y/n)?"

You whispered a weak 'yes' knowing that he was referring to the wet sounds his member was making, "You know why my cock makes this sound when I slide it on your pussy, little girl?" Your grasp on his tee tightened, as you tried to hold back your noises.

"Cause I'm embarrassingly wet for you, Coach Winchester!" He chuckled in your ear, tapping on your clit with his length and making you buck your hips into him, "Damn straight you are, tell me one last time what you want, (Y/n), and I'll give it to you!"

You rubbed yourself up and down against him, loving the way his eyes fluttered shut and the groan that left his lips, "I want you to push your big cock inside me and fuck me hard. Fuck me like no one else can, Dean, please!"

"What did you call me?" Your eyes widened for a second, you hadn't even noticed your slip, but apparently Dean did, "Coach Winchester! Please, please, Coach, I can't take it anymore!"

Dean smiled down at you, pecking your lips and you knew that was your Dean and not Coach Winchester, before he pushed back inside of you, making you moan and shut your eyes at the amazing burn his stretch was providing.

He set a fast pace, pistoning his hips into you as you groaned and cursed, clawing at his desk in an attempt to ground yourself to something, anything, "T-this what you n-needed to see me for?"

"Yes-ffffuck! Please, Coach, don't stop!" He slowed down for a moment and the next second your top was being ripped apart, the fabric forgotten at your sides as Dean's hand grabbed your boob and squeezed it, adding to your pleasure.

"Fuckin-you're so God-damned tight...s-so wet!" You nodded, capturing his lips in a bruising kiss as you felt a tight ball beginning to form in your lower stomach, tightening with each one of his hard thrusts into you.

"P-please, Coach! I-I'm so-ah fffuck! Harder, p-please h-hharder!" Dean complied, taking you with all he had, thrusting his hips hard and fast as his lips latched on one of your nipples, sucking and biting just like you loved him to do.

You were a needy mess, begging him to make you come as you tugged on his hair and pushed your chest closer to him, and he grinned against your skin, bringing his free hand down to flick your clit and before you knew it, you were coming.

Your back arched off the desk, eyes wide open as you moaned his name followed by a string of curses. You felt your muscles tense and your walls clamped down on him, pulling him over the edge with you.

Dean came with a groan of your name, his hand gripping your hips so tight you knew there would be bruises blossoming on your skin in the morning.

He kept thrusting his hips, slower this time, just helping you both down from your highs, before he collapsed back on the chair, pulling you with him.

A slow grin spread on your lips as you felt him softening inside of you, your core still slightly throbbing and making him hiss, before he lifted you up a little and slipped out of you; his come dripping down your thighs and onto his.

You nuzzled his neck as you both brought your breathing under control, before you felt his hand under your chin, lifting it until you locked your (e/c) eyes on his, "Well, Miss (L/n), that was awesome! Thank you, baby!"

"I don't know what you're thanking me for, I'm the one who just got fucked into next week!" He chuckled as you relaxed back onto his chest, kissing your forehead and hugging you closer to him, "I know you did it to indulge my cheerleader thing!"

You hummed your acknowledgment, pressing kisses all over his chest as he caressed up and down your back, "Mmmhm, let me know if you have any more fantasies you'd like to live out, I'll be glad to make them come true!"

You winked at him and his eyes darkened again, his tongue snaking out to wet his lips, "Oh, sweetheart, I got plenty of those, but first, I think I should make one of your dirty fantasies come true!"

You felt your cheeks turn beet red and you averted your gaze, feeding Dean's curiosity, "Tell you what, let's get dressed up and out of this place, and then you can tell me what's this thing that got you all flushed, baby girl!"

You slowly nodded your head and he ducked his own to peck your lips, before he pulled up his pants and you grabbed your underskirt. He ended up giving you his jacket to wrap around yourself since he'd ripped your top and then you made your way to Baby.

You reached the motel and after you took turns taking a shower, Dean waited until Sam went to get you all some food, before he plopped down on the bed next to you and let his finger trace your stomach, "Gonna tell me what your dirty little fantasy is, (Y/n)?"


End file.
